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Copilot AI commented Nov 15, 2025

Addresses user request for troubleshooting guidance when VS Code Remote SSH connections over Tailscale fail or become unstable.

Changes

Added comprehensive troubleshooting section to docs/tailscale-setup.md covering:

  • Server process issues: Commands to kill/uninstall hung VS Code server instances via Command Palette
  • Tailscale connectivity: Ensuring persistent connections (Run unattended, disable key expiry), status checks, restart procedures
  • SSH keepalive configuration: ServerAliveInterval/ServerAliveCountMax/TCPKeepAlive settings for ~/.ssh/config
  • Long-running device stability: Log/PID cleanup commands, disk space checks, periodic reboot recommendations
  • Network mount workarounds: Relocating VS Code server to local directories when home is on NFS/SMB
  • Alternative Remote-SSH settings: useLocalServer, useExecServer, enableRemoteCommand toggles

Screenshot

Troubleshooting section

Content sourced from official VS Code, Microsoft, and Tailscale documentation plus community best practices.

Warning

Firewall rules blocked me from connecting to one or more addresses (expand for details)

I tried to connect to the following addresses, but was blocked by firewall rules:

  • docs.python.org
    • Triggering command: /opt/hostedtoolcache/Python/3.12.12/x64/bin/python /opt/hostedtoolcache/Python/3.12.12/x64/bin/sphinx-build -M html . _build (dns block)
  • docs.scipy.org
    • Triggering command: /opt/hostedtoolcache/Python/3.12.12/x64/bin/python /opt/hostedtoolcache/Python/3.12.12/x64/bin/sphinx-build -M html . _build (dns block)
  • matplotlib.org
    • Triggering command: /opt/hostedtoolcache/Python/3.12.12/x64/bin/python /opt/hostedtoolcache/Python/3.12.12/x64/bin/sphinx-build -M html . _build (dns block)
  • numpy.org
    • Triggering command: /opt/hostedtoolcache/Python/3.12.12/x64/bin/python /opt/hostedtoolcache/Python/3.12.12/x64/bin/sphinx-build -M html . _build (dns block)
  • pandas.pydata.org
    • Triggering command: /opt/hostedtoolcache/Python/3.12.12/x64/bin/python /opt/hostedtoolcache/Python/3.12.12/x64/bin/sphinx-build -M html . _build (dns block)
  • pio1.local
    • Triggering command: /opt/hostedtoolcache/Python/3.12.12/x64/bin/python /opt/hostedtoolcache/Python/3.12.12/x64/bin/sphinx-build -M html . _build (dns block)
  • pyscaffold.org
    • Triggering command: /opt/hostedtoolcache/Python/3.12.12/x64/bin/python /opt/hostedtoolcache/Python/3.12.12/x64/bin/sphinx-build -M html . _build (dns block)
  • scikit-learn.org
    • Triggering command: /opt/hostedtoolcache/Python/3.12.12/x64/bin/python /opt/hostedtoolcache/Python/3.12.12/x64/bin/sphinx-build -M html . _build (dns block)
  • setuptools.pypa.io
    • Triggering command: /opt/hostedtoolcache/Python/3.12.12/x64/bin/python /opt/hostedtoolcache/Python/3.12.12/x64/bin/sphinx-build -M html . _build (dns block)
  • www.sphinx-doc.org
    • Triggering command: /opt/hostedtoolcache/Python/3.12.12/x64/bin/python /opt/hostedtoolcache/Python/3.12.12/x64/bin/sphinx-build -M html . _build (dns block)

If you need me to access, download, or install something from one of these locations, you can either:

Original prompt

This section details on the original issue you should resolve

<issue_title>Issue on page /tailscale-setup.html troubleshooting vs code remote ssh with tailscale</issue_title>
<issue_description>https://ac-training-lab.readthedocs.io/en/latest/tailscale-setup.html#vs-code-configuration

Help me by looking up various ways to help troubleshoot a bad vs code remote ssh server (e.g., needing to kill the remote before trying again, ensuring it has high uptime via tailscale, etc.)</issue_description>

Comments on the Issue (you are @copilot in this section)


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Co-authored-by: sgbaird <45469701+sgbaird@users.noreply.github.com>
Copilot AI changed the title [WIP] Troubleshoot VS Code remote SSH connection issues with Tailscale Add VS Code Remote SSH troubleshooting guide for Tailscale connections Nov 15, 2025
Copilot AI requested a review from sgbaird November 15, 2025 03:36
Copilot finished work on behalf of sgbaird November 15, 2025 03:36
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Issue on page /tailscale-setup.html troubleshooting vs code remote ssh with tailscale

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